Water → 5-Phenylethynyl-2-ureido-thiophene-3-carboxylic Acid Amide

HRID 2223361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223361
Br[C:2]1[S:6][C:5]([NH:7][C:8]([NH2:10])=[O:9])=[C:4]([C:11]([NH2:13])=[O:12])[CH:3]=1.C(N(CC)CC)C.[C:21]1([C:27]#[CH:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C=O)C.[Cu]I.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:21]1([C:27]#[C:28][C:2]2[S:6][C:5]([NH:7][C:8]([NH2:10])=[O:9])=[C:4]([C:11]([NH2:13])=[O:12])[CH:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

9

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 111846265-Bromo-2-ureidothiophene-3-carboxamide

Produkt 1

HCID 100167795-Phenylethynyl-2-ureido-thiophene-3-carboxylic Acid AmideAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5-Bromo-2-ureido-thiophene-3-carboxylic acid amide (0.264 g, 1.0 mmol), copper (I) iodide (0.005 g), triphenyl phosphene (0.030 g, 15 mole %), palladium acetate (0.010 g, 5% mole %), triethyl amine (1 mL) and phenylacetylene (0.1 g, 1.1 mmol) in DMF (4 mL) was added to a 9 mL reaction vial. The reaction vial was sealed and heated to 100° C. in a Smith Microwave Synthesizer for 20 min. Water (5 mL) and ethyl acetate (20 mL) were added to the reaction mixture, the organic phase was separated and then washed with brine (2×10 mL) and water (1×10 mL), and dried over anhydrous magneium sulfate. After filtration, the solvent was removed under vacuum and the crude residue was taken into DMSO (5 mL) and purified utilizing a Gilson preparative HPLC to give the above titled compound as a light brown solid (0.050 g, 0.18 mmol, 18% yield). LC-MS [M+H]+ m/z 286.

Aufarbeitung

  1. customThe reaction
  2. customvial was sealed
  3. customthe organic phase was separated
  4. washwashed with brine (2×10 mL) and water (1×10 mL)
  5. dry with materialdried over anhydrous magneium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was removed under vacuum
  8. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-44a9e0d2b5184a4e92ecfc07f334e9f8
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375131B2

Notizen zur Reaktion

Wird geladen…